2-Amino-6-Chloropyrazine → 6-Methoxypyrazin-2-amine

HRID 1396902Notes

Reaction equation

HRID 1396902 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1.[CH3:9][O-:10].[Na+]>CO>[CH3:9][O:10][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 1184582-Amino-6-ChloropyrazineHCID 10942334Sodium Methoxide

Product 1

HCID 48681936-Methoxypyrazin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-chloro-2-pyrazinamine (200 mg, 1.544 mmol) and sodium methoxide (250 mg, 4.63 mmol) in methanol (3.9 ml) was heated to 130° C. via a microwave reactor for 60 min. The crude product mixture was purified by RP-HPLC to give 6-(methyloxy)-2-pyrazinamine (154 mg, 1.231 mmol, 80% yield). MS (ES+) m/z 125.8 (MH+).

Workup

  1. customThe crude product mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-1f6f7b2d301e46ad9aa36d9fe744280b
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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